tert-butyl 3-((S)-3-tert-butoxy-5-oxo-1-((S)-pyrrolidin-3-yl)-2,5-dihydro-1H-pyrrol-2-yl)propanoate | 1433503-38-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl 3-((S)-3-tert-butoxy-5-oxo-1-((S)-pyrrolidin-3-yl)-2,5-dihydro-1H-pyrrol-2-yl)propanoate
• 英文别名: tert-butyl 3-[(2S)-3-[(2-methylpropan-2-yl)oxy]-5-oxo-1-[(3S)-pyrrolidin-3-yl]-2H-pyrrol-2-yl]propanoate
• CAS: 1433503-38-8
• 化学式: C₁₉H₃₂N₂O₄
• 分子量: 352.474
• InChiKey: GBQBULIWXZJZRE-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-5-benzylpyrrolidine-2,4-dione 、 tert-butyl 3-((S)-3-tert-butoxy-5-oxo-1-((S)-pyrrolidin-3-yl)-2,5-dihydro-1H-pyrrol-2-yl)propanoate 在 palladium 10% on activated carbon 、 氢气 、 原甲酸三甲酯 作用下， 以 异丙醇 为溶剂， 反应 5.0h， 以55%的产率得到
  参考文献：
  名称：

  Expanding the Scope of Oligo-pyrrolinone–Pyrrolidines as Protein–Protein Interface Mimics

  摘要：

  Oligo-pyrrolinone-pyrrolidines (generic structure 1) have the potential to interfere with protein-protein interactions (PPIs), but to reduce this to practice it is necessary to be able to synthesize these structures with a variety of different side chains corresponding to genetically encoded proteins. This paper describes expansion of the synthetic scope of 1, the difficulties encountered in this process, particularly issues with epimerization and slow coupling rates, and methods to overcome them. Finally, spectroscopic and physicochemical properties as well as proteolytic stabilities of molecules in this series were measured; these data highlight the suitability of oligo-pyrrolinone-pyrrolidines for the development of pharmacological probes or pharmaceutical leads.

  DOI：

  10.1021/jo400323k
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 tert-butyl 3-((S)-3-tert-butoxy-5-oxo-1-((S)-pyrrolidin-3-yl)-2,5-dihydro-1H-pyrrol-2-yl)propanoate
  参考文献：
  名称：

  Expanding the Scope of Oligo-pyrrolinone–Pyrrolidines as Protein–Protein Interface Mimics

  摘要：

  Oligo-pyrrolinone-pyrrolidines (generic structure 1) have the potential to interfere with protein-protein interactions (PPIs), but to reduce this to practice it is necessary to be able to synthesize these structures with a variety of different side chains corresponding to genetically encoded proteins. This paper describes expansion of the synthetic scope of 1, the difficulties encountered in this process, particularly issues with epimerization and slow coupling rates, and methods to overcome them. Finally, spectroscopic and physicochemical properties as well as proteolytic stabilities of molecules in this series were measured; these data highlight the suitability of oligo-pyrrolinone-pyrrolidines for the development of pharmacological probes or pharmaceutical leads.

  DOI：

  10.1021/jo400323k

文献信息

• Expanding the Scope of Oligo-pyrrolinone–Pyrrolidines as Protein–Protein Interface Mimics
  作者：Arjun Raghuraman、Dongyue Xin、Lisa M. Perez、Kevin Burgess

  DOI：10.1021/jo400323k

  日期：2013.5.17

  Oligo-pyrrolinone-pyrrolidines (generic structure 1) have the potential to interfere with protein-protein interactions (PPIs), but to reduce this to practice it is necessary to be able to synthesize these structures with a variety of different side chains corresponding to genetically encoded proteins. This paper describes expansion of the synthetic scope of 1, the difficulties encountered in this process, particularly issues with epimerization and slow coupling rates, and methods to overcome them. Finally, spectroscopic and physicochemical properties as well as proteolytic stabilities of molecules in this series were measured; these data highlight the suitability of oligo-pyrrolinone-pyrrolidines for the development of pharmacological probes or pharmaceutical leads.